Chinese Journal of Organic Chemistry >
Advances in Research on 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Structure and Pyrazole-Containing Herbicides
Received date: 2017-05-21
Revised date: 2017-06-22
Online published: 2017-07-04
Supported by
Project supported by the National Key Technology Research and Development Program of the Ministry of Science and Technology (No. 2014BAD20B01), the National Natural Science Foundation of China (No. 21372093, 21672079) and the Chinese Universities Basic Scientific Research (No. CCNU15A02011).
4-Hydroxyphenylpyruvate dioxygenase (HPPD), a target for green herbicide discovery, has recently attracted a large number of famous scientists attention owing to controlling efficacy of resistant weeds. The structures of HPPD, inhibitors binding sites, mode of action and their metabolites are summarized. The current commercial and developing pyrazole-containing herbicides of HPPD are analyzed. Based on combining theory and practical application, a direction to find or design a new inhibitor is also oriented.
He Bo , Wang Dawei , Yang Wenchao , Chen Qiong , Yang Guangfu . Advances in Research on 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Structure and Pyrazole-Containing Herbicides[J]. Chinese Journal of Organic Chemistry, 2017 , 37(11) : 2895 -2904 . DOI: 10.6023/cjoc201705031
[1] Yang, G. F. Curr. Pharm. Des. 2014, 2, 0685.
[2] Hrens, H.; Lange, G.; Müller, T.; Rosinger, C.; Willms, L.; van Almsick, A. Angew. Chem., Int. Ed. 2013, 52, 9388.
[3] Beaudegnies, R.; Edmunds, A. J. F.; Fraser, T. E. M.; Hall, R. G.; Hawkes, T. R.; Mitchell, G.; Schaetzer, J.; Wendeborn, S.; Wibley, J. Bioorg. Med. Chem. 2009, 17, 4134.
[4] Zhou, Y. Y.; Li, Z. M. World Pestic. 2013, 35, 1(in Chinese). (周蕴赞, 李正名, 世界农药, 2013, 35, 1.)
[5] Yin, Z. D.; Zhang, L.; Chen, H.; Wang, Y. Y.; Ouyang, G. P. Liaoning Chem. Ind. 2016, 45, 739(in Chinese). (尹振东, 张苈, 陈洪, 涂红, 王圆圆, 欧阳贵平, 辽宁化工, 2016, 45, 739.)
[6] Deng, H. X.; Qian, Y. Y.; Chen, Y. P. Zhejiang Chem. Ind. 2012, 43, 1(in Chinese). (邓红霞, 钱跃言, 陈亚萍, 浙江化工, 2012, 43, 1.)
[7] Yang, W. C.; Lin, H. Y.; Yang, S. G.; Liu, W. N.; Yang, G. F. Chin. J. Pestic. Sci. 2013, 15, 139(in Chinese). (杨文超, 林红艳, 杨盛刚, 刘万年, 杨光富, 农药学学报, 2013, 15, 139.)
[8] Lee, M. H.; Zhang, Z. H.; MacKinnon, C. H.; Baldwin, J. E.; Crouch, N. P. FEBS Lett. 1996, 393, 269.
[9] Ling, T.; Shiu, S.; Yang, D. Bioorg. Med. Chem. 1999, 7, 1459.
[10] Ellis, M. K.; Whitfield, A. C.; Gowans, L. A.; Auton, T. R.; Provan, W. M.; Lock, E. A.; Lee, D. L.; Smith, L. L. Chem. Res. Toxicol. 1996, 9, 24.
[11] Endo, F.; Awata, H.; Tanoue, A.; Ishiguro, M.; Eda, Y.; Ttani, K.; Matsuda, I. J. Biol. Chem. 1992, 267, 24235.
[12] Barta, I. C.; Böger, P. Pest. Sci. 1996, 48, 109.
[13] Garcia, I.; Rodgers, M.; Lenne, C.; Rolland, A.; Sailland, A.; Matringe, M. Biochem. J. 1997, 325, 761.
[14] Yang, C.; Pflugrath, J. W.; Camper, D. L.; Foster, M. L.; Pernich, D. J.; Walsh, T. A. Biochemistry 2004, 43, 10414.
[15] Ruetschi, U.; Odelhog, B.; Lindstedt, S.; Barros-soderling, J.; Persson, B.; Jornvall, H. Eur. J. Biochem. 1992, 205, 463.
[16] Johnson-Winters, K.; Purpero, V. M.; Kavana, M.; Moran, G. R. Biochemistry 2005, 44, 7189.
[17] Fritze, I. M.; Linden, L.; Freigang, J.; Auerbach, G.; Huber, R.; Steinbacher, S. Plant Physiol. 2004, 134, 1388.
[18] Brownlee, J. M.; Johnson-Winters, K.; Harrison, D. H. T.; Moran, G. R. Biochemistry 2004, 43, 6370.
[19] Richaed, W. L.; Jane, W. B. Crit. Rev. Toxicol. 2013, 43, 185.
[20] Lin, J.; Li, Z. G.; Zou, J. W.; Lu, S. Y. Acta Chim. Sinica 2012, 70, 1309(in Chinese). (林军, 李祖光, 邹建卫, 陆绍永, 化学学报, 2012, 70, 1309.)
[21] Wójcik, A.; Broclawik, E.; Siegbahn, P. E. M.; Borowski, T. Biochemistry 2012, 51, 9570.
[22] Neidig, M. L.; Decker, A.; Choroba, O. W.; Huang, F.; Kavana, M.; Moran, G. R.; Spencer, J. B.; Solomon, E. I. Proc. Natl. Acad. Sci.U. S. A. 2006, 103, 12966.
[23] Raspail, C.; Graindorge, M.; Moreau, Y.; Crouzy, S.; Lefebvre, B.; Robin, A. Y.; Dumas, R.; Matringe, M. J. Biol. Chem. 2011, 286, 26061.
[24] Riggins, C. W.; Peng, Y.; Stewart, C. N.; Tranel, P. J. Pest Manag. Sci. 2010, 66, 1042.
[25] Wójcik, A.; Broclawik, E.; Siegbahn, P. E. M.; Lundberg, M.; Moran, G.; Borowski, T. J. Am. Chem. Soc. 2014, 136, 14472.
[26] Lin, J. F.; Sheih, Y. L.; Chang, T. C.; Chang, N. Y.; Chang, C. W.; Shen, C. P.; Lee, H. J. PLoS One 2013, 8, e69733.
[27] Diebold, A. R.; Brown-Marshall, C. D.; Neidig, M. L.; Brownlee, J. M.; Moran, G. R.; Solomon, E. I. J. Am. Chem. Soc. 2011, 133, 18148.
[28] Wang, D. W. Ph.D. Dissertation, Central China Normal University, Wuhan, 2015(in Chinese). (王大伟, 博士论文, 华中师范大学, 武汉, 2015.)
[29] Kimura, F. Jpn. Pestic. Inform. 1984, 45, 24.
[30] Rene, L.; Michael, K.; Joachim, G.; Michael, R.; Von, D. W. US 20030149276, 2003[Chem. Abstr. 2003, 136, 118263].
[31] Schmitt, M.; van Almsick, A.; Preuss, R.; Willms, L.; Auler, T.; Bieringer, H.l; Thuerwaechter, F. WO 2001/074785, 2001[Chem. Abstr. 2001, 135, 288780].
[32] Lian, L.; Zheng, Y. R.; He, B.; Peng, X. G.; Jin, T.; Cui, Q. CN 105218449, 2016[Chem. Abstr. 2016, 164, 175130].
[33] Peng, X. G.; Jin, T.; Zhang, J. Y.; Zhao, D.; Cui, Q. CN 1568549, 2016[Chem. Abstr. 2016, 165, 162543].
[34] Yamaoka, K.; Nakagawa, M.; Ishida, M. J. Pestic. Sci. 1987, 12, 209.
[35] Wolf, J. K.; Termes, S. C. Fed. Regist. 2013, 78, 48068.
[36] Mikio, Y.; Yasumi, K.; Takashi, M.; Atsushi, N. JP 2013040141, 2013[Chem. Abstr. 2013, 158, 381770].
[37] Wang, D. W.; Lin, H. Y.; Cao, R. J.; Chen T.; Yang, S. G.; Chen, Q.; Yang, W. C.; Yang, G. F. J. Agric. Food Chem. 2015, 63, 5587.
[38] Wang, D. W.; Lin, H. Y.; Cao, R. J.; Yang, S. G.; Chen, T.; He, B.; Chen, Q.; Yang, W. C.; Yang, G. F. Acta Chim. Sinica 2015, 73, 29(in Chinese). (王大伟, 林红艳,曹润洁, 杨盛刚, 陈涛, 何波, 陈琼, 杨文超, 杨光富, 化学学报, 2015, 73, 29.)
[39] Xu, Y. L.; Lin, H. Y.; Cao, R. J.; Ming, Z. Z.; Yang, W. C.; Yang, G. F. Bioorg. Med. Chem. 2014, 22, 5194.
[40] Xu, Y. L.; Lin, H. Y.; Ruan, X.; Yang, S. G.; Hao, G. F.; Yang, W. C.; Yang, G. F. Eur. J. Med. Chem. 2015, 92, 427.
[41] Lei, K.; Hua, X. W.; Tao, Y. Y.; Liu, Y.; Liu, N.; Ma, Y.; Li, Y. H.; Xu, X. H.; Kong, C. H. Bioorg. Med. Chem. 2016, 24, 92.
[42] Matthias, W. Bioorg. Med. Chem. 2009, 17, 4221.
[43] Wang, B. L.; Li, Q. N.; Zhan, Y. Z.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Phosphorus Sulfur, Silicon Relat. Elem. 2014, 189, 483.
[44] Wang, B. L.; Wu, J.; Liu, Q. X.; Li, Y. H.; Song, H. B.; Li, Z. M. Phosphorus Sulfur, Silicon Relat. Elem. 2015, 190, 66.
/
| 〈 |
|
〉 |
